Diprotonative stabilization of ring-opened carbocationic intermediates: conversion of tetrahydroisoquinoline to triarylmethanes
Diprotonative stabilization of ring-opened carbocationic intermediates: conversion of tetrahydroisoquinoline to triarylmethanes
复制标题
DOI：
10.1039/d0cc01969k
复制
发表时间：
2020-07-28
影响因子：
4.9
通讯作者：
Kurouchi, Hiroaki
中科院分区：
文献类型：
--
作者：
Kurouchi, Hiroaki
超强酸促进四氢异喹啉转化为三芳基甲烷经历了C-N键断裂、Friedel-Craft烷基化、C-O键断裂和亲电芳香族酰胺化等一系列反应。阳离子的形成对稳定开环碳阳离子中间体具有重要作用，这是双质子化在反应机理中的新作用。
Superacid-promoted conversion of tetrahydroisoquinolines to triarylmethanesviatandem reactions of C-N bond scission, Friedel-Crafts alkylation, C-O bond scission, and electrophilic aromatic amidation was developed. Dication formation was important for stabilizing the ring-opened carbocationic intermediate, which is a new role for diprotonation in reaction mechanisms.